Winchester Vacation Rentals, St. Louis: house rentals & more

Scroll through and select from vacation rentals in Winchester to find one that's perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include WiFi and a hot tub. Whatever you're looking for, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.

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Find the best place to stay - Winchester

Lovely master bedroom with fireplace and sitting area.

The St. Charles Guest House, lovely historic home, fun for families and groups

Sleeps 8 · 3 bedrooms · 2 bathrooms

Top rated rentals - Winchester

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Charming Kirkwood cottage

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Book a vacation rental for your Winchester getaway

Experience the unique character of Winchester with a stay in a vacation home rental. This city has something for everyone. Six Flags St. Louis and St. Louis Zoo are just a couple of the must-sees in the area. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Winchester

Are you searching for attractions to visit in the area? Venture out of your cozy vacation rental and experience everything that makes Winchester a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

Six Flags St. Louis (9.5 mi / 15.3 km)
St. Louis Zoo (13.2 mi / 21.2 km)
Chesterfield Sports Fusion (7.1 mi / 11.4 km)
Hidden Valley Ski Resort (7.8 mi / 12.5 km)
Grant's Farm (9.8 mi / 15.8 km)
Bellerive Country Club (5.4 mi / 8.6 km)

Exploring the natural landscape of Winchester

Whether you're an active traveler or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Winchester. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

Route 66 State Park (7 mi / 11.3 km)
Lou Fusz Soccer Complex (7.7 mi / 12.4 km)
Forest Park (13.9 mi / 22.4 km)
Tower Grove Park (14.2 mi / 22.8 km)
Katy Trail (14.3 mi / 23 km)
Missouri Botanical Gardens and Arboretum (14.6 mi / 23.5 km)

Traveling to and around Winchester

The nearest airport is in St. Louis, MO (SUS-Spirit of St. Louis), located 8.1 mi (13 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into St. Louis Lambert Intl. Airport (STL), which is 13.7 mi (22 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Winchester?

The average price for a vacation home in Winchester is determined by a number of factors, like season, property type and length of stay. Whether you prefer a sprawling house with room for friends and family or a quaint cottage just enough for two, just enter your dates of travel to see some great-value stays.

How much does it cost to rent a beach house in Winchester?

Prices for beach houses in Winchester may vary depending on the type and size of the property and when you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to view vacation rental options and prices. From there you can use our filter tool to narrow your search results by amenities, ratings, nearby activities and more.

How old do you have to be to rent a vacation rental in Winchester?

Age restrictions can vary across properties on Vrbo, so double-check the rules of the vacation home in Winchester you're considering. But usually, it's 16, 18 or 21.

How long can I rent a vacation rental in Winchester for?

It's up to the Winchester property. To browse a list of options offering extended stays, just enter your dates and guest number into Vrbo's search page. You can look forward to having the whole place to yourself, as well as comforts such as air conditioning, a fully-equipped kitchen and a backyard where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.